Triethylamine → 2,5-dichloro-N-(1-methyl-1-phenylethyl)nicotinamide

HRID 21340

Reaction equation

HRID 21340 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[C:12]([NH2:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([NH:21][C:12]([CH3:14])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 27999962,5-Dichloro-nicotinoyl chloride

Product 1

HCID 866283382,5-dichloro-N-(1-methyl-1-phenylethyl)nicotinamideYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 16, 2,5-dichloropyridine-3-carbonylchloride (669 mg, 3.19 mmol) was dissolved in dichloromethane (13 mL), and the solution was treated with cumylamine (0.505 mL, 3.51 mmol), triethylamine (0.667 mL, 4.79 mmol) and DMAP (39.0 mg, 0.319 mmol), followed by purification by slurry using diisopropylether/hexane to obtain 2,5-dichloro-N-(1-methyl-1-phenylethyl)nicotinamide (926 mg, yield 94%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-0164a6f54d57470083813ea7da61ae35
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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